2-Propanethiol → [3-(4-Bromo-2-isopropylsulfanylmethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

HRID 656746Notes

Reaction equation

HRID 656746 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[CH2:22]Br)[CH:7]=1)[CH3:2].[CH3:25][CH:26]([SH:28])[CH3:27].[H-].[Na+]>O1CCOCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][C:16]=2[CH2:22][S:28][CH:26]([CH3:27])[CH3:25])[CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 63642-PropanethiolHCID 24758Sodium hydrideHCID 58237498[3-(4-Bromo-2-bromomethyl-phenoxy)-4-methoxy-phenyl]acetic acid ethyl ester

Product 1

HCID 58372820[3-(4-Bromo-2-isopropylsulfanylmethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

[3-(4-Bromo-2-bromomethyl-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester (0.4 g, 0.87 mmol) and 2-propanethiol (0.08 g, 1.0 mmol) were combined in 1,4-dioxane (20 mL). Sodium hydride (60% in mineral oil; 0.04 g, 1.0 mmol) was added, and the reaction was stirred at room temperature for 20 minutes. The mixture was worked up to give the title compound.

Sources & evidence

ORD record
ord-0a6cc1aa3b9a45408a969be98c68bf37
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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